Breaking the Prude (Shimoseka)

A/N: Breaking the Prude was a commissioned one-shot originally written back in December of 2018. Posting it now for people to enjoy!

Themes: Mind Break, Rough Sex, Fucked Silly

-x-X-x-

He's nervous, of course. But he's also full of optimism. He really wants to make a good impression, and this is his best chance, right? If ever Tanukichi Okuma had a chance of getting with Anna Nishikinomiya, then it was by impressing her mother, Sophia. So, given the chance to meet with the older woman, even if it was in private, Tanukichi couldn't very well pass that up, now could he? When the chance to spend the holidays in the Nishikinomiya Mansion reared its head, he had to take it, there was no question about that.

Though, he would have preferred to be meeting Sophia with Anna at his side, if only for support. The young woman was the nicest person he'd ever met, so surely, she'd have his back if anything went wrong. Alas, it was not to be. Instead, he was being led through the mansion's halls by a servant, who had already instructed him to keep his mouth shut and his head down. That, Tanukichi could do… or try to do, anyways.

As the servant finally opens the door and the young man walks into the room after receiving a gesture to do so, the first thing he notices is the smell of wine that assaults his senses. Then the door closes behind him, just as he's laying eyes upon Sophia Nishikinomiya for the first time, at least in person.

"You. You're the brat, right? … hic!"

Oh god, she's drunk. That's the first thing that runs through Tanukichi's mind, as he takes in the sight of Sophia, his crush's mother, sitting upon a couch with her legs crossed and a mostly empty wine glass in her hand. On the table before her is a bottle that's already half-empty, and when Tanukichi lays his eyes on it, Sophia's gaze follows. She curses under her breath and belatedly pulls the wine bottle down off of the table, putting it at her feet as if that hides it from view or something.

"Sit."

Tanukichi is a little impressed that she doesn't slur that word, but regardless, he's also far too nervous not to obey. Sitting down on the couch opposite of her, the coffee table between them, Tanukichi places his hands on his knees and grips them tightly as he tries not to stare. But at the same time, would it not be rude for him to not make eye contact?

That was the problem though. If he tried to look at her face, he found himself studying the flushed, red state of her cheeks rather than staring into her slightly glazed over eyes. There was no denying it… Sophia Nishikinomiya was drunk. She was inebriated… and that did not change the fact that she held his future in her hands.

"You're the shpawn of that dirty joke terrorist, yesh? Zenjoru Okuma… hic!"

There was a bit of the slur. Tanukichi winces, but ultimately nods.

"That's um… t-that's right. But I'm nothing like him, of course! I don't… I don't act like he did!"

He really didn't. He tried his best not to, anyways. Despite his extensive knowledge of all things lewd and dirty, learned at a very young age, Tanukichi had, long ago, realized that such knowledge did not actually help him in any way. People ostracized him for what he knew, for how debauched his mind could get. So Tanukichi bottled up such thinking and did his best to act perfectly normal at all times.

Now if only he could convince Mrs. Nishikinomiya of that. Sophia peers at him searchingly, even as she drunkenly sways side to side. Then, she brings her wine glass to her lips and tries to drink from it. Only, she's been absently doing that between speaking since he arrived, and this time, she finds the glass is once again empty.

With a growl, the older woman reaches down and snatches up the bottle from by her feet, standing in the same moment as she begins to pour herself another glass while at the same time trying to walk around the coffee table. It's… it's akin to watching a train crash in slow motion. Tanukichi realizes what's about to happen a second before it does, and he just doesn't have enough time to dodge out of the way or do anything but widen his eyes.

As Sophia aims to loom over him all intimidating like, while also getting more wine in her body, she clips the corner of the coffee table on Tanukichi's side by accident. To her credit, the drunken MILF manages to catch herself, so she doesn't fall… but it's at the expense of the by-now full glass of wine in her left hand, which goes tumbling forward, emptying its expensive contents ALL over Tanukichi's head and shirt.

He ends up positively soaked in the red wine, sitting there on the couch, frozen and dripping wet, unsure what to do. Sophia, meanwhile, is peering down at the mess she's made with a frown that's growing progressively bigger.

"… Up! Get off my couch… hic! You're gonna ruin it!"

That makes sense to Tanukichi, so he hurriedly jumps up. Sophia's nose wrinkles as she finds himself eye to eye with the tall young man, and her frown develops even further.

"You're filthy. Go get cleaned up."

Even drunk, it's clear she's used to giving commands. Tanukichi, meanwhile, is all too happy to follow this one. Swallowing thickly, the young man vacates the room, quickly finding a servant who yet again tells him to be silent before guiding him to the nearest bath.

Meanwhile, back in the parlor, Sophia frowns, some small part of the normally straight-laced woman knowing she'd just made an absolute fool of herself. Still, it wasn't entirely her fault. She'd been on her third glass of wine when news that Anna had invited a boy over for the holidays had reached her. Too late to stop by that point, now wasn't it? And with her husband gone on a 'business trip' it was just Sophia and Anna and now this… this Tanukichi Okuma for New Years.

On top of that, there's no denying that the beautiful woman has been overworked lately. She's been run ragged… mostly by herself, by her own initiatives. And though she'll never admit it, those same initiatives have led to a great deal of agitation, due to the fact that her and her husband have not had sex in quite a long time.

It's a sacrifice though, one Sophia was willing to make. To keep her daughter safe, to protect Anna's purity… the world needed to know that lewdness and depravity would not be tolerated! She'd done quite a lot to make that a reality, to make sex anathema. And she'd done a good job of it too. But there was no denying that the lack of sex was beginning to take its toll on the MILF… even if SHE would still try to deny it till the end of her days.

However, her attempt to gauge whether or not Tanukichi was a good boy in spite of his father or just the son of an ero-terrorist… it hadn't worked out in her favor, now had it? Blinking dumbly down at her wine glass and the mostly empty bottle in each of her hands, Sophia scowls again and sets both down on the coffee table. She goes to move out of the room, only to stop and turn back around to look at the only MOSTLY empty wine bottle.

… One more glass couldn't hurt, right? Despite this thought, the empty wine glass never sees more use, as the silver-haired MILF grabs up the bottle and drinks straight from it. She's going to need it, if she's having to spend the holidays fighting off this young man so he doesn't do anything untoward to her daughter!

-x-X-x-

Tanukichi's optimism is dead and buried now, even as he takes a quick shower to get the wine out of his hair while his clothes run through the wash. It's just a simple rinse-off, so it wouldn't have taken him long, but Tanukichi considered the bathroom to be a bit of a sanctuary in the den of a dragoness. Surely, nobody would disturb him here, right? That meant he had time to think.

Sophia Nishikinomiya was nothing like he thought she would be, at least in person or in private or whatever. She was… it was… that whole encounter had been almost surreal. Tanukichi didn't know what was going on, but he knew that he needed to be the PERFECT gentleman if he wanted to survive this upcoming New Year. He just had to remain calm, and things would get back to normal soon enough.

Though by this point, he was beginning to wish Anna had never heard him say he wasn't celebrating the holidays simply because he had no one to celebrate them with. She'd immediately invited him to her place for New Year, and he, in his infinite stupidity, had accepted like it was a good idea. It was not. It was a bad idea, an extremely bad idea, and Tanukichi realized that now, even as he tried and failed to figure out exactly what he was going to do next.

Still, he couldn't stay in the shower forever, now could he? With a sigh, Tanukichi shuts off the water and finally steps out, grabbing a towel and drying himself off with it. It's big, white, and fluffy, and honestly, it's the best towel that Tanukichi has ever used… so yes, he does enjoy it for a bit longer than is strictly necessary.

As a result, the young man is JUST managing to tie the towel off around his waist to preserve his modesty when, contrary to his previous thoughts on this being a sanctuary, the door to the bath suddenly swings open, and in walks the MILF of the hour herself, Sophia Nishikinomiya. Obviously, Tanukichi immediately finishes covering his junk, even as he lets out an eep that draws the MILF's drunken eye.

It doesn't help that she's no longer dressed at this point. Oh sure, she's not COMPLETELY nude, but she is… she is dressed down. And by dressed down, Tanukichi means she's wearing the sexiest, hottest set of black lacy lingerie that he's EVER seen. Her gorgeous body fits into the underwear perfectly, her curves and her bust and her hips a-and… and…

"P-Pervert!"

Tanukichi's eyes widen at that, even as Sophia points an accusatory, victorious finger in his direction. Flustered beyond belief, the young man reacts by doing what is, in hindsight, undoubtedly the worst thing he could have done. But it's instinct. So, without further ado, in the face of Sophia's accusatory finger, Tanukichi raises both hands in the air in the classic surrender pose, eyes wide and head shaking back and forth.

Unfortunately for him, his body is betraying him even in that moment. Specifically, his cock is rapidly growing thicker and bigger in the face of the absolute vision of lewd beauty standing before him. And the towel he's wrapped around his waist is not prepared for the unfortunate boner he's very quickly sporting. The tucking he did to make it stay pops free, and just like that, the only thing covering him up and protecting his modesty unravels and falls off of Tanukichi's body, leaving him standing there COMPLETELY naked.

For a moment, there's absolute silence as both Tanukichi and Sophia look down the length of his body, to where his cock, erect and almost looking angry, is now pointed directly at the older woman. Sophia moves first, a knowing, vicious smirk etched across her drunken features even as she stalks forward, swaying from side to side in a not-so-seductive manner.

Her hand lashes out, and she misses at first. But Tanukichi isn't exactly trying to dodge at this point, frozen in indecision as he is. On her third attempt, Sophia manages to grab his dick in her hand and grip it tightly in a way that only manages to turn him on further as she scowls down at it.

"Bad! Bad cock! Bad, lewd, naughty dick!"

He can hardly believe what's happening. Especially when Sophia starts to jack him off, as if she's trying to punish him while continuing to scold his dick for being hard and erect in her hand. The drunken MILF is literally pointing his cock up at her face now as she stands there in her black lingerie, just jerking his member and telling it off at the same time.

Does she not understand what she's doing to him? Tanukichi opens his mouth to try and tell her, but the words die in his throat, because before he can say a single thing, she thumbs his tip and sends him right over the edge. As Sophia pulls her thumb away, it's like she's popped the cork on a fresh wine bottle. Tanukichi's cum shot positively LEAPS out of his cock, pulsing up the length of his shaft as it departs his churning balls.

Quite a lot of it strikes Sophia in the chest, with a bit hitting her chin, her lips, and even her cheeks and nose. The MILF freezes up as this happens, eyes wide as she stares down at his ejaculating dick, cum hitting her in multiple places. Her scolding dies down, and she slowly reaches up to slide her fingers through the cum on her face. In that moment, Tanukichi is sure that he's done for. This is it, this is the end.

And yet, that's not what happens next. There's no scream of outrage, no claim that he raped her with his cum or something like that. Servants don't rush in to tackle him to the ground for the police to pick up. His life doesn't end… at least not in that moment. Because instead of outrage, the drunken MILF before him slips the messy finger into her mouth and slurps it clean, and Tanukichi watches as Sophia develops the strongest blush he's ever seen, along with a phenomenon he didn't think was actually a real thing. The MILF's pupils turn into hearts right before his eyes, and all Tanukichi can do is gape as Sophia settles in to begin licking up his seed, cleaning herself off with her fingers and tongue.

She moans throughout these next few moments, and once she's done, Tanukichi just can't hold back anymore. Those full, pouty lips of hers, now that they're cleaned of his cum… they're just begging to be kissed. Grabbing up the sexy MILF, Tanukichi pulls Anna's mom close and kisses the ever-living daylights out of her.

In her drunkenness, Sophia reciprocates. The makeout session is forceful and passionate and tongue-filled and rough, but most of all, its short. Because Tanukichi is still hard and when he pulls back, there's only ONE thing he wants now.

"Bedroom. Now."

Sophia blinks stupidly for a moment, before looking down at his cock again and blushing profusely. But she does it all the same. She leads him out of the bath and to the Master Bedroom, and luckily, they don't pass a single servant along the way. As soon as they get there though, as soon as they're inside, Tanukichi spins Sophia back around and kisses her again.

To his surprise, she's a little bit more resistant this time, squirming in his embrace, though not actively trying to pull away. When they separate, Tanukichi can immediately tell why… she's beginning to sober up, slowly but surely, and the first inklings of doubt are appearing on her face. But he's too far in now to stop… this is going all the way, damn the consequences.

Sophia doesn't fight him as he strips her of her bra and her panties, the black lingerie falling to the wayside as Tanukichi leans in to play with her breasts, nibbling and kissing and lapping at them with his mouth. Sophia moans, and then stumbles backwards when he gives her a push towards the bed. What follows is a bit of wrestling, but soon enough Tanukichi has them both in position, his tongue delving deep into the MILF's cunt while his hard cock hovers just inches from her face.

The ball is in her court now. She's on top, he's on bottom, and as Tanukichi starts thoroughly eating the hot, sexy MILF out, he's fully prepared for a complete lack of reciprocation. As it turns out, that's not what happens. It seems despite slowly sobering up, Sophia can't help herself. She moans a few times, takes in a few whiffs of Tanukichi's musk… and then finally sucks on his cockhead, slurping at his precum as it leaks out of his dick tip.

Bobbing up and down on his cock, the MILF gyrates her hips across Tanukichi's face, but he's not stopping for nothing. His hands grope and squeeze at Sophia's ass cheeks and inner thighs, and his tongue delves deeper and deeper into her sopping wet cunt. Eventually, he brings her off with just that tongue, and Sophia's moans reverberate up his shaft as she climaxes, squirting pussy juices all over his face.

Unable to hold back, Tanukichi cums again as well, and though Sophia tries to swallow as much as she can, most of it ends up spilling out of the sides of the MILF's mouth, though she's quick to slurp it back up, even as he pulls her off of him and spins her onto her back. In moments, while Sophia is busy dealing with his cum load, Tanukichi positions himself between her legs, finally ready to do the deed.

His cockhead presses against her slit for the first time, but in a moment of stark clarity, Sophia stops him, her hands pressing into his front.

"W-Wait…"

It's not a scream of outrage or utter denial or insults about his dick or his family, so Tanukichi does indeed stop and wait, looking down at her curiously. The older woman blushes deeply at having this younger man atop her, taking control, about to fuck her. But that doesn't stop her for reaching over to the bedside table and pulling a condom out of the top drawer.

"We… w-we need to use protection."

For a moment, Tanukichi is admittedly tempted to throw the condom in her face. Was it not Sophia Nishikinomiya who had so effectively campaigned against young teenagers using condoms that teen pregnancies had gone UP, instead of down? According to her constant rants and speeches, abstinence was supposed to be better than birth control, because people his age weren't supposed to ever have sex anyways.

And now here she was, like the hypocrite she was, giving him a condom so that he didn't knock HER up. Tanukichi certainly has a lot to say about that, but he doesn't say it for now. No, there'll be another chance later. For the time being, the young man unwraps the condom and pulls it down his cock, before giving Sophia no warning as he shoves his covered cock RIGHT into her drooling quim.

The MILF's pale blue eyes go wide and then roll halfway back in her head as her mouth forms into an O. Tanukichi can't deny that it feels pretty good as well, and he quickly begins fucking her, his hands gripping tightly at her thighs as he pounds in and out of her tight, warm cunt with wild abandon. It's obvious to him now what's been going on here. Anna's mom has been repressed and deprived all this time. She's very clearly been quietly horny for a good, long while… and that means it's up to him to draw every bit of perversion and lewdity out of her.

Who better than the son of an ero-terrorist to break the woman who equated eroticism with terrorism in the first place? Tanukichi had come to the Nishikinomiya estate today for one reason, but now he found himself here in Sophia's bed for another reason entirely, even as he plows the hot, sexy MILF senseless, groping and squeezing her gorgeous breasts all the while.

Both eventually cum, Sophia more than once before Tanukichi finally blows his load on the inside of the condom. But even as the sexy MILF lays there, panting and out of breath… he's not done. Leaning in, Tanukichi takes Sophia's lips and kisses them in quite the domineering manner, making out with his crush's MILF of a mom even as he begins to fuck her again, uncaring of the sticky feeling of the used condom still wrapped around his cock.

As soon as Sophia has cum again, Tanukichi pulls out and forces the older woman onto her hands and knees before taking her from behind in doggystyle. Sophia gasps at this, and tries to protest, but her own moans and cries of pleasure as he fucks her nice and deep swallow those weak protests right up, leaving her incoherent and unintelligible, even as she continues to cum her brains out from the good, hard dicking that Tanukichi is giving her.

Sophia climaxes several more times before Tanukichi cums again, but this time, he doesn't continue right off the bat, not with TWO loads of his seed now filling the condom. Pulling out of the exhausted fat-assed MILF, Tanukichi pushes Sophia over onto her back with a foot, and then pulls the used condom off of his messy cock, before bringing it to her lips.

"You had no problem swallowing my cum earlier, right?"

Blushing brightly, but unable to deny his words, Sophia takes the condom from his grasp and delicately brings the open end to her lips with one hand, while tipping the filled bottom up with the other. His thick, viscous seed, white and hot even now, slides right down the MILF's throat as she perversely swallows it right then and there.

As soon as she's done, Tanukichi's cock is in her face too, slapping her a couple times before smearing what's left of his seed across her lips. He doesn't even have to say anything with this one. Still blushing profusely, Sophia nonetheless opens up and sucks his cock clean, her cheeks suctioning in as her pale eyes remain fixed on his face the entire time.

Tanukichi is grinning like a loon now, and honestly, he actually FEELs a bit like an ero-terrorist at this point. He can only imagine how proud his father would be. Not that Tanukichi was doing this for him… he was doing it for HIMSELF.

Sitting down on the bed again, the young man pulls the naked MILF he's fucked twice now into his lap. His barebacked cock rubs against her slit, hot-dogging it as he leans his chin on her shoulder and gropes her breasts from behind. Sophia moans, squirming and wiggling in his grasp, even as she stares down at his leaking prick, so close to her needy honey pot.

"You… y-you need another condom…"

Tanukichi pauses at that, and hums slightly.

"… No."

That causes the MILF to freeze up in shock.

"W-What?! No?! You… you can't fuck me without a condom on, y-young man!"

Her attempt at trying to regain some sort of control over the situation while she's sitting in his lap moaning like a bitch in heat and getting treated like one as well is laughable. But Tanukichi has a plan. Smirking, he just shrugs, which she can feel thanks to his chin on her shoulder and his hands on her tits.

"Then I guess I just won't fuck you, Mrs. Nishikinomiya. After all, abstinence is the best form of birth control, isn't it?"

Having her own words thrown back in her face does the trick. Sophia's mouth opens and closes like a gold fish, but she never quite manages to get a full sentence out after that. Tanukichi hums again, and then reaches down and grabs her by her thighs, squeezing them harshly as he lifts her up and places her just atop the head of his cock. If he lets go, or if she tries to pull out of his grasp, she's almost CERTAINLY going to be impaled on his member.

"I suppose if you WANTED me to fuck you without the condom, I could do so. Just have to say the word!"

This was his revenge, or at least part of it. And when Sophia finally nodded, he didn't wait or demand a verbal agreement, despite saying she had to 'say the word'. Nah, a nod was good enough. Dropping the beautiful MILF down on his cock has to be one of the greatest moments of Tanukichi's life, especially when she immediately climaxes on his shaft, squealing like a stuck pig and shaking and spasming along his length.

Tanukichi quickly begins bouncing the sexy older woman up and down on his dick, not waiting, not hesitating, and certainly showing her NO mercy. This prudish bitch deserved every bit of pleasure, and he was going to GIVE it to her. That's exactly what Tanukichi proceeds to do, and he makes the ensuing fuck last long enough for Sophia to fall completely, her lustful moans and her constant orgasms eventually leading to the moment he's been waiting for.

"D-Do it! Cum inside! Pump me full of your baby seed, Tanukichi! Knock me up! DO IT!"

And do it he does. Filling Sophia Nishikinomiya with his cum may not have been Tanukichi's original intention for this holiday, but he's not going to stop now. His seed pumps directly into the MILF's womb, and Sophia immediately begins to cum as well, her eyes rolling fully back in her skull as her tongue lolls out of her mouth and she moans throatily and wantonly.

In that moment, she's nothing but a slut, nothing but HIS slut… and yet, Tanukichi is JUST getting started. As he pulls Sophia's somewhat limp body off of his cock, he contemplates what to do with her next… because his hard-on is still raging, and he knows she's gonna get it until he's tapped the fuck out.

-x-X-x-

Time passes, and lots of creampies follow. Tanukichi ends up continuing things with a titjob, which Sophia, her eyes full hearts now and her moans constant and lustful, eagerly obeys him on. She wraps her fat, full breasts around his cock, only moaning all the louder when he insults them and labels her a cow for having such LEWD and PERVERTED titties. She accepts every bit of his verbal abuse like the whore she now is, and Tanukichi takes advantage of the power he has over her, all thought of making a 'good impression' on Anna's mother gone from the bestial boy's mind.

He makes sure to fill her womb near to bursting with a few more creampies via doggystyle too. He wants her to get pregnant with his baby. He wants her to get knocked up. She'll grow heavy with his child and judging by the way Sophia moans loudly and lewdly every time he suggests that to her, she likes the idea of him breeding her just as much.

Things end with one final fuck, this time standing, though by this point the MILF's legs are incredibly shaky and weak. Tanukichi holds her up all the same, pinning her against the bathroom sink counter and forcing her to watch her own lustful expression of pure ecstasy in the mirror. He's also recording it quite obviously, but does Sophia mind that? No, no she does not.

"If I want, everyone in the world will know what a slutty bitch you are, Sophia… do you want that?"

"Oooh, it would… it w-would ruin me… but I don't care! E-Except, my daughter… it would h-hurt Anna! F-For her sake, please don't let it out! I'll… I'll do ANYTHING!"

Despite it seeming like blackmail, the lust inherent in the MILF's voice, the arousal in her expression and the way her hips are bouncing back against him as he thrusts his cock inside of her cream-filled quim again and again… certainly make it feel like she's just looking for an excuse. Still, Tanukichi likes Anna well enough too. He doesn't want to hurt her in any way. So, for that reason, he won't destroy Sophia by uploading this recording or any other he makes to the internet. Instead, he'll just keep them for his own private use… and perhaps as a bit of insurance to make sure that the MILF he's now addicted to his cock stays in line.

Regardless, he's got a bitch to breed, and that's exactly what Tanukichi does as he continues to fill Sophia with his cock, displacing some of the cum from her cunt, though not from her cream-stuffed womb. Still, when he finally does cum moments later once again, filling her with even more of his seed, he replaces any of that displaced ejaculate, while at the same time getting an excellent video of Sophia's O face, the MILF's eyes crossed and her mouth a big wide O as she climaxes and seizes up and shakes from the pleasure.

Chuckling darkly, Tanukichi finishes up the recording and tucks his phone away before grabbing Sophia by her hair, fisting it into a ponytail as he uses his other hand to hold onto her side. Then, he turns them both around and begins walking Sophia back into the Master Bedroom, pounding into her from behind still every step of the way, only his grip on her keeping her from collapsing into a mind-broken, well-fucked heap right before his feet.

Not yet though… not yet. He's not done exacting his punishment from the bitch who effectively ruined his life quite yet. He's not done BY FAR.

-x-X-x-

When the phone rings sometime later, Tanukichi reaches over and answers it, feeling extremely confident.

"Nishikinomiya Residence, Tanukichi Okuma speaking."

"Ah… Tanukichi? I see you're settling in okay over there!"

It's Anna on the other end. Chuckling slightly, Tanukichi looks down at the young woman's mother, who even now is biting down on the bedding before her, stained with his cum and trying to keep quiet as he hammers into her from behind, his balls slapping her clit and his cock making squelching noises in and out of her cunt.

"Your mother has been very… welcoming, Anna."

"Oh! I'm so glad to hear that, I was a little worried… well, no matter! I should be home in about an hour, will you let mama know?"

Tanukichi's grin is positively wicked as he hums into the receiver, covering up the smack of his palm against Sophia's ass by doing so.

"Sure, I'll let you know. And don't worry Anna, I'll be sure to take reeeal good care of your mom until you get back. Alright?"

"Thanks, Tanukichi, I knew I could count on you!"

He's chuckling again as he hangs up and puts the phone back down on its cradle. Meanwhile, his cock begins to slide out of Sophia… but the woman rises up immediately to latch onto him, spinning about and then re-impaling herself on his dick as she moans throatily, her face the picture-perfect expression of wanton perversion now.

"More… please, Master. Mooooore~"

Tanukichi just smiles. That, he can do.

-x-X-x-

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